Private Sailing Charters

Top Rated Private sailing Charters in St Thomas

Before You Book · Important Notes
Gratuity Not Included

20% is the recommended minimum. Cash is preferred. Plan ahead — ATMs are not always easy to find when you're on the water.

Valid Passport Required

Every passenger visiting the British Virgin Islands must carry a valid passport — including children and babies. No exceptions. Half-day charters typically do not go to the BVI.

Customs Fees Not Included

Budget an additional $75–$85 per person for BVI customs and departure fees. Cash preferred.

Fuel Surcharge Applies

Expect a fuel surcharge of $150–$650 depending on the size of the boat and destinations. Your captain will confirm the amount before disembarking.

Safety Gear Provided

All charters are required to carry life vests. Most also include floats, snorkel gear, bottled water, and ice.

Drinks & Snacks

Not all charters stock alcoholic beverages or snacks. If you have something specific in mind, you're encouraged to bring your own drinks and snacks on board.

What to Bring
Bathing Suit & Towel

You'll be in and out of the water all day. Bring a cover-up or extra layer for the ride back — the wind on the water can surprise you. Some charters provide towels, many don't, so bring your own to be safe.

Reef-Safe Sunscreen or Rash Guard

No aerosols on board. Sun exposure on the water is more intense than it feels — a rash guard is a great alternative or addition. Apply sunscreen before you board and bring extra for reapplication.

Cash & Card

Bring both. Cash is essential for gratuity and customs fees. A card is useful for extra drinks, food, or shopping at your stops. Don't count on finding an ATM once you're on the water.

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Most Popular

From

$2,000

📍 OASIS COVE MARINA, ST. THOMAS 🧍 12 GUESTS ⏱ 6-7 hours

Freedom - 45' Lagoon catamaran - USVI FULL-DAY

Freedom's got four distinct zones to spread out on — forward cockpit, flybridge, aft cockpit, salon — so a full boat never feels crowded, and there's always a different view to take in. Your captain sails you around the best of St. Thomas and St. John, whether that's a snorkel and pizza stop at Christmas Cove, a swim with turtles at Maho Bay, or lunch at Lovango Cay over some of the clearest water in the islands. It's a day built around the sailing itself — good wind, good company, and no shortage of places worth stopping. Base price coveres 6 guests.

This Charter Includes

  • Captain + crew
  • Open bar with ice, water, juice, soda, beer & liquor
  • Morning snack (fruit & muffins) + afternoon snack (charcuterie, crudite, humms, chips & salsa)
  • Snorkel gear & floats
  • Fresh water rinse
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Most Popular

From

$1,295

📍 Sapphire Beach Marina 🧍 12 guests ⏱ {DURATION}

Blue Dream - 55' Jeanneau Sailing Yacht - usvi full-day

Blue Dream is the largest monohull daysailer around, which means she covers ground fast without giving up an inch of comfort. Six hours is enough time to reach further than most charters get — usually out toward St. John National Park and the surrounding cays — with a professional captain and mate handling the sailing so you can just enjoy it. It's a fully private trip, so the itinerary really is whatever you want it to be, whether that means chasing down a few snorkel spots or finding one perfect anchorage and staying put. Base price covers 4 guests.

This Charter Includes

  • Captain + crew
  • Open bar with ice, water, soda, beer, wine & liquor
  • Shaded seating + on-board restroom
  • Snorkel gear, foats & paddle boards
  • Prepared hot lunch
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Most Popular

From

$895

📍 Sapphire Beach Marina 🧍 12 guests ⏱ 3 hours

Blue Dream - 55' Jeanneau Sailing yacht - usvi half-day

Three hours is plenty of time to make it out to St. John National Park or Christmas Cove — home of the famous floating pizzeria, Pizza Pi, if that's calling your name. It's an easygoing option that works especially well with kids along, and the crew's known for finding the good snorkel spots, not just the closest ones. A shorter day on the water, same open bar and the same attention to getting you somewhere worth being. Base price coveres 4 guests.

This Charter Includes

  • Captain + crew
  • Open bar with ice, water, soda, wine, beer & liquor
  • Shaded seating + on-board restroom
  • Snorkel gear & floats
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Most Popular

From

$1,900

📍 Red Hook, St. Thomas 🧍 12 guests ⏱ 6 or 8 hours

SP1 & SP2 - Fountaine Pajot Liparis - USVI or bvi Full-Day

Sail Pending and her sister ship are matching 45′ Fountaine Pajot Liparis — roomy, easy on the eyes, and set up for a full day of drifting around wherever you point them. Choose USVI (six or eight hours) or BVI over to Jost Van Dyke (eight hours), and let the crew string together beaches, coves, or a beach bar stop along the way. Lunch can go either way: pull up at a famous beach bar, or have the crew cater it right on deck. Base price covers 6 guests.

This Charter Includes

  • Captain + Crew
  • Light breakfast (fruit & muffins) + afternoon snack (fresh-baked cookies & light snacks)
  • Large cooler stocked with soda, beer, water & ice + open bar
  • Snorkel gear, SUP + floats
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From

$1,500

📍 Compass point marina, st. thomas 🧍 12 guests ⏱ 6 hours

Sea Level - 50' Ketch-rigged monohull - usvi full-day

A truly unique experience aboard a classic sailing yacht with plenty of time to snorkel a clear-water spot, nibble on hors d'oeuvres, and work through a stocked open bar. Swing by Pizza Pi in Christmas Cove if the timing's right, or indulge in Captain Fancy's Low Country Boil. There's a floating oasis to lounge on, Turkish cotton towels, reef-safe sunscreen, an air-conditioned head onboard — and Pedro the Pirate Dog will probably come say hello at some point too. Base price covers 4 guests.

This Charter Includes

  • Captain + crew
  • Air conditioned cabin & bathroom + fresh water rinse
  • Snacks and hors d'oeuvres
  • Snorkel gear + floats + SUP + reef-safe sunscreen + towels<
  • Ice, water & sodas + beer, wine & liquor Open Bar
  • Option to add on Low Country Boil w/ Shrimp & Lobster
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Most Popular

From

$750

📍 Compass point marina, st. thomas 🧍 12 guests ⏱ 3.5 hours

Sea Level - 50' ketch-rigged monohull - usvi half-day

3.5 hours aboard a classic sailing yacht is plenty of time to snorkel a clear-water spot, nibble on hors d'oeuvres, and work through a stocked open bar. Swing by Pizza Pi in Christmas Cove if the timing's right, or pre-order from An Hour Late for something more substantial. There's a floating oasis to lounge on, Turkish cotton towels, reef-safe sunscreen, an air-conditioned head onboard — and Pedro the Pirate Dog will probably come say hello at some point too. Base price covers 4 guests

This Charter Includes

  • Captain + crew
  • Air conditioned cabin & bathroom + fresh-water rinse
  • Snacks and hors d'oeuvres
  • Snorkel gear + floats + SUP + reef-safe sunscreen + towels<
  • Ice, water & sodas + beer, wine & liquor Open Bar
Book Now